Red halogenized dye and process of making.



' mg agents,

the powdery according to the UNITED STATES PATENT ouricu.

ALBRECHT SCHMIDT AND ERNST BRYK, or, H6CHST-ON4THE-MAIN, GERMANY, .AS-srenoas To FARBW RKE VORM. MEISTER LUCIUS & BRiiNING, or I-IfiCI-IST-ON-THE-MAIN, GERMANY, A CORPORATION or GERMANY.

RED HALOGENIZED DYE -AND PROCESS OF MAKING.

No Drawing.

Specification of Letters Patent. Application filed July 8, 1908. SerialNo. 442,626.

Patented July 12, 1910.

-ment of the yellowish-red -di-alkoxythioindigos with halogens orhalogen eliminatbromin in the cold, or by gently heating with chlorin,or, with special advantage, by treating with sulfurylchloriol (accordingto the U. S. Patent No. 812598 very fast and valuable halogenized dyestus areobtained,

This is a surprising fact in, several i espects. It was neither to beexpected that the alkoxylroups when halogenized would behaveindiiferently (indeed when halogenized more strongly for instance atraised temperature there will be a decomposition), nor could it beexpected that in this way pure red and not violet dyestuffs could beobtained.

Example I: 1 part by wei ht of it-diethoxythioindigo C H O S :4: 2 1 isstirred with'8 parts of bromin. while cooling. The mixture is allowed tostand for a while, blackish mass is diluted with carbon tetnachlorid, isfiltered oil, and is then treated with a solution of bisulfite andboiled with alcohol. The dyestuff thus obtained dyes wool and cottonpure red shades of excellent fastness. Inbromination, dissolving agentssuch as nitrobenzene,"carbon tetrachlorid, water, sulfuric acid, etc.may be employed. Gentle heat may also be applied desired degree ofbromination.

Example II: 1 part by weight of lc-diethoxythioindigo is stirred'with 4.parts of sulfuryl-chlorid and allowed to stand for a while. Here, also,dissolving agents, such as for instance by treating with nitrobenzene,carbon tetrachlorid, etc. may be added. Further, in converting themixture, it may be gently heated according to the desired degree ofhalogenation. The reaction mass is diluted with carbon tetrachlorid,filtered off and the )rcduct washed with alcohol. The dyestufi thusobtained dyes in the vat shades of a more intense red than the parentproduct.

ment with chlorin gas. In the place of the di-ethoxythioindigos, theirleuco compounds, and other ll-oxyethers of the thioindigo, or theirleuco compounds,

may be used.

Having now we claim is:

1. The process for, the manufacture of red dyestufls, which. consists intreating 4:- oxyethers of the thioindigo with a halogenizing reagent ata moderate temperature.

2. As new products, the herein-described red halogenizedv dyestuffs,which are insoluble in water, diluted acids, diluted alkalies, alcoholand ether; but soluble in hot nitrobenzene with a yellowish-red colorand in concentrated sulfuric acid with a blue color, forming with analkaline solution of hydrosulfid a yellow vat, from which cotton is dyedin very fast red tints.

3. As a new product, halogenized 4-diethoxythioindig'o, which isinsoluble in water, diluted acids, diluted alkalies, alcohol and other;but soluble in hot nitrobenzene with a yellowish-red color and inconcentrated sulfuric acid with a blue color, forming with an alkalinesolution of hydrosul'fid a yellow vat, from which cotton is dyed in redtints.

In testimony whereof, we afiix our signatures in presence of twowitnesses.

ALBRECHT SCHMIDT.

ERNST BRYK.

described our invention, what Witnesses: v

JEAN GRUND, CARL GRUND.

Similar dyestuffs are obtained by treat

